Cherry Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Cherry Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $820, price is now $643 per person
$643
per person
Dec 31 - Jan 5
found 8 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,309, price is now $869 per person
$869
per person
Dec 31 - Jan 5
found 8 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The hotel is beautiful and the staff are attentive, friendly and welcoming. The hotel and our accommodations were very neat and clean. The hotel is in a great location downtown within walking distance of many attractions, shops, and restaurants. Highly recommend this hotel for anyone looking for a place to stay in downtown Chicago.
Reviewed on Nov 8, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,182, price is now $842 per person
$842
per person
Dec 31 - Jan 5
found 8 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,466, price is now $1,054 per person
$1,054
per person
Dec 21 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Blackstone, Autograph Collection
Downtown Chicago
Price was $1,237, price is now $921 per person
$921
per person
Dec 21 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Nice property but a little worn.mattresses were not that comfortable .Some staff were great, others not so much.
Reviewed on Nov 8, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,274, price is now $1,001 per person
$1,001
per person
Dec 21 - Dec 29
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Top Hotel Deals
Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
20.88 km from city center
Book a stay at this golf hotel in Utica. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ...
La Quinta Inn & Suites by Wyndham Peru Starved Rock St Park
4389 Venture Dr Peru IL
9.96 km from city center
Book a stay at this business-friendly hotel in Peru. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
Days Inn by Wyndham Oglesby/ Starved Rock
120 N Lewis Ave Oglesby IL
18.43 km from city center
Book a stay at this business-friendly hotel in Oglesby. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Super 8 by Wyndham Ottawa Starved Rock
500 East Etna Rd. Ottawa IL
32.12 km from city center
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms ...
Comfort Inn Ottawa Starved Rock Area
120 W. Stevenson Road Ottawa IL
31.75 km from city center
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Best Western Oglesby Inn
900 Holiday Street Oglesby IL
18.58 km from city center
Book a stay at this business-friendly hotel in Oglesby. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
Super Rest Inn
2929 N Main St Princeton IL
21.49 km from city center
Stay at this motel in Princeton. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Bureau ...
Fairfield Inn & Suites Peru
4385 Venture Dr Peru IL
9.99 km from city center
Book a stay at this business-friendly hotel in Peru. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
Quality Inn Peru near Starved Rock State Park
5240 Trompeter Road La Salle IL
9.63 km from city center
Stay at this hotel in La Salle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Super 8 by Wyndham Peru Starved Rock State Park
1851 May Rd La Salle IL
9.61 km from city center
Book a stay at this business-friendly hotel in La Salle. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Quality Inn & Suites Mendota near I-39
1307 Kailash Dr Mendota IL
18.92 km from city center
Stay at this hotel in Mendota. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Tri-County ...
AmericInn by Wyndham Princeton IL
2120 Claude Bailey Pkwy Princeton IL
20.94 km from city center
Book a stay at this business-friendly hotel in Princeton. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our ...
Holiday Inn Express & Suites Ottawa by IHG
2850 Columbus Street Ottawa IL
32.08 km from city center
Book a stay at this business-friendly hotel in Ottawa. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Dec 22 - Wed, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$253 Roundtrip, found 6 days ago
$253
Roundtrip
found 6 days ago
Sat, Dec 19 - Wed, Dec 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$258 Roundtrip, found 6 days ago
$258
Roundtrip
found 6 days ago
Tue, Dec 22 - Sat, Dec 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$353 Roundtrip, found 6 days ago
$353
Roundtrip
found 6 days ago
Tue, Dec 22 - Sat, Dec 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$383 Roundtrip, found 6 days ago
$383
Roundtrip
found 6 days ago